2,4-Dibromobenzaldehyde

General procedure: To a 50mL round-bottom flask fitted with a magnetic stirringbar, intermediate 5 (3.0 g, 1 mmol) and the solution of substituted benzaldehyde (1.2 mmol) in anhydrous ethanol (10 mL) were added in order, then the round-bottom flask was sealed and placed in the synthetic reactor and reacted under microwave irradiation at 90 C with 150 W for 20 min. Upon completion of the reaction (monitored by TLC), the mixture was concentrated under vacuum and purified after recrystallization from ethanol to obtain the target compounds 6a-6u. The physical characteristics, IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis datafor all the target compounds 6a-6u are shown in Supplementary Materials, and the data for the representative compound 6s are shown below.General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.General procedure: A solution of anhydrous Cu(OAc)2 (1.8 mg, 0.01 mmol) andligand 7d (4.0 mg, 0.01 mmol) in MTBE (1 mL) in a 10mL test tubeequipped with a magnetic stirring bar was stirred at room temperaturefor 30 min. Next, 20 mL DABCO (5M dissolved in n-propanol)was added, followed by stirring for 5 min. After the aldehyde(0.2 mmol) was added to the reaction mixture, we stirred the mixture at 10 C for 2 min, and then 2-nitropropane (180 mL, 2 mmol) was added to the tube. The reaction was stirred at 10 Cand monitored by TLC. After the complete reaction, the chiral product was separated by flash column chromatography (PE/EA 9/1). Enantiomeric excesses were determined by HPLC chiralcolumn.To a 250 mL RBF was added Example 361.0 (3.06 g, 8.76 mmol) in 2-methyltetrahydrofuran (22 mL). n-Butyllithium, (2.5M solution in hexanes, 4.20 mL, 10.51 mmol) was then added under N2 at -78 C. The reaction mixture was stirred at -78 C for 10 mm and then left at RT for 20 mm. 2, 4- Dibromobenzaldehyde (2.54 g, 9.63 mmol) in 2-methyltetrahydrofuran (22 mL) was then added dropwise under N2 at -78 C. The reaction mixture was stirred at -78 C for 1 h. LCMS analysis indicated formation of the desired product. The reaction was quenched with a saturated aqueous solution of NH4C1. The reaction mixture was diluted with a saturated solution of NH4C1 and extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give a light-yellow solid which was purified by silica gel chromatography (a gradient of 0% to 100% EtOAc in DCM). This provided the title compound Example 143.1 (4.9 g, 7.99 mmol, 91 % yield) as a white solid which was a mixture of diastereomers. LCMSESI (pos.), m/z: 634.0 (M+Na)t

Molecular Weight:263.91
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:263.86084
Monoisotopic Mass:261.86289
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes